In a blender, combine vanilla ice cream, milk, molasses, ginger, cinnamon, cloves, and chocolate syrup. Tip: For a thicker shake, use slightly less milk.

Blend on high until smooth and creamy, about 30 seconds. Tip: Scrape down the sides if needed for even blending.

Add brownie chunks and pulse 2-3 times just to incorporate (you want visible chunks!). Tip: Freeze brownies for 15 minutes first for cleaner cuts.

Pour into glasses, top with whipped cream, and garnish with crushed gingerbread cookies. Tip: Chill glasses beforehand for a frosty presentation.